diff --git a/src/vs/platform/actions/browser/toolbar.ts b/src/vs/platform/actions/browser/toolbar.ts
index c76b6eeb57a0f..cbce9d98d0ef3 100644
--- a/src/vs/platform/actions/browser/toolbar.ts
+++ b/src/vs/platform/actions/browser/toolbar.ts
@@ -8,6 +8,7 @@ import { IToolBarOptions, ToolBar } from 'vs/base/browser/ui/toolbar/toolbar';
 import { IAction, Separator, SubmenuAction, toAction, WorkbenchActionExecutedClassification, WorkbenchActionExecutedEvent } from 'vs/base/common/actions';
 import { coalesceInPlace } from 'vs/base/common/arrays';
 import { BugIndicatingError } from 'vs/base/common/errors';
+import { Emitter, Event } from 'vs/base/common/event';
 import { DisposableStore } from 'vs/base/common/lifecycle';
 import { localize } from 'vs/nls';
 import { createAndFillInActionBarActions } from 'vs/platform/actions/browser/menuEntryActionViewItem';
@@ -283,6 +284,9 @@ export interface IMenuWorkbenchToolBarOptions extends IWorkbenchToolBarOptions {
  */
 export class MenuWorkbenchToolBar extends WorkbenchToolBar {
 
+	private readonly _onDidChangeMenuItems = this._store.add(new Emitter<this>());
+	readonly onDidChangeMenuItems: Event<this> = this._onDidChangeMenuItems.event;
+
 	constructor(
 		container: HTMLElement,
 		menuId: MenuId,
@@ -309,7 +313,10 @@ export class MenuWorkbenchToolBar extends WorkbenchToolBar {
 			super.setActions(primary, secondary);
 		};
 
-		this._store.add(menu.onDidChange(updateToolbar));
+		this._store.add(menu.onDidChange(() => {
+			updateToolbar();
+			this._onDidChangeMenuItems.fire(this);
+		}));
 		updateToolbar();
 	}
 
diff --git a/src/vs/workbench/contrib/interactiveEditor/browser/interactiveEditorWidget.ts b/src/vs/workbench/contrib/interactiveEditor/browser/interactiveEditorWidget.ts
index c83e3b23ede54..148a62f09a863 100644
--- a/src/vs/workbench/contrib/interactiveEditor/browser/interactiveEditorWidget.ts
+++ b/src/vs/workbench/contrib/interactiveEditor/browser/interactiveEditorWidget.ts
@@ -290,6 +290,7 @@ export class InteractiveEditorWidget {
 			}
 		};
 		const statusToolbar = this._instantiationService.createInstance(MenuWorkbenchToolBar, this._elements.statusToolbar, MENU_INTERACTIVE_EDITOR_WIDGET_STATUS, workbenchToolbarOptions);
+		this._store.add(statusToolbar.onDidChangeMenuItems(() => this._onDidChangeHeight.fire()));
 		this._store.add(statusToolbar);
 
 		// preview editors
@@ -301,6 +302,7 @@ export class InteractiveEditorWidget {
 		this._elements.message.tabIndex = 0;
 		this._elements.statusLabel.tabIndex = 0;
 		const markdownMessageToolbar = this._instantiationService.createInstance(MenuWorkbenchToolBar, this._elements.messageActions, MENU_INTERACTIVE_EDITOR_WIDGET_MARKDOWN_MESSAGE, workbenchToolbarOptions);
+		this._store.add(markdownMessageToolbar.onDidChangeMenuItems(() => this._onDidChangeHeight.fire()));
 		this._store.add(markdownMessageToolbar);
 	}